But the draw request and fulfillment process really shouldn't be all that painful. 

There is nothing about how long you need to occupy the property for.So unless our lender puts a demand on us I see no problems legally in occupying each property for any amount of time to fulfill the requirement, then rinse and repeating this process up to our full entitlements, so long as the lender is willing to keep giving us loans.

If someone does not fulfill their contribution, how does the partnership handle that issue?

I'm sure there are many more experiences where the contractor hasn't fulfilled their scope of work and gotten away with rushing the project to meet the deadline, And, I don't want to be as naive to say that I'm that 1% who can have complete quality/operational control, but I'm confident I can establish a system and hire independent inspectors to review the contractor's work. 

Are there any others in CT which can fulfill these requirements?

Hang out with others that are doing what you want to do and invest your $25-$50,000 in real estate vs education. 

While this is a great and highly motivating goal, most people are either clueless or incorrect in their belief as to what is required to obtain this “lifestyle”.Understanding of the “how to” get there is further obscured by the misleading, and often patently false “pathways” sold by real estate educational MARKETING companies as workshops, upsold to association memberships, upsold to mentorships.

anyone have any experience with Walter Wofford and his short term rental education programs?

If the owner submits a completed application before the servicer starts the state foreclosure process, the servicer can't foreclose until the following occurs:the borrower doesn’t qualify for, or rejects, the lender’s loss mitigation options, orthe borrower accepts a loss mitigation offer but fails to fulfill its requirements."

I obviously had not educated myself well before diving in.